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How to Investigate Suspicious Microsoft 365 Sign-Ins and Audit Activity

By Freedom251 Team · · 11 min read

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Investigate an unusual Microsoft 365 sign-in as a sequence, not a single alarming location: identify the user and authentication flow, compare it with that account’s normal behavior, correlate Entra and Microsoft 365 audit records, then validate and contain the account when evidence supports compromise. IP geography and a risk alert are clues—not proof—so the conclusion must come from the complete event chain and your tenant’s retained records.

What a suspicious Microsoft 365 sign-in investigation must establish

A useful investigation answers four questions in order:

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  • Who authenticated, and was the identity a person, service principal, or managed identity?
  • How did the request authenticate, including the client, device, authentication sequence, and Conditional Access result?
  • Where and when did the request appear, allowing for VPN, mobile-provider routing, and time-zone differences?
  • What happened afterward in directory, Microsoft 365, data, or administrative activity?

A sign-in that looks unusual in isolation may be legitimate travel, a new device, a mobile carrier address, or a delegated workload. Conversely, a successful sign-in that looks ordinary can still precede mailbox, directory, or data changes. Treat the sign-in as the starting point for an evidence timeline.

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Prepare access and preserve the right evidence

Access and retention determine what you can prove. Check that the investigator can view the relevant records before drawing conclusions, and record the tenant’s retention and log-routing configuration as part of the case.

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Use the least privilege that fits the task

Investigation need Role or entitlement identified in Microsoft guidance
View sign-in and audit logs Reports Reader is the least privileged role specified for this risk-investigation use case.
View Microsoft Entra ID Protection risk reports Global Reader is identified for viewing these reports.
Use the full Microsoft Entra ID Protection feature set Entra ID P2 or Entra Suite is required; verify the current tenant entitlement.

Role names, assignments, licensing, portal labels, and available records can change. Confirm them in the affected tenant rather than assuming that a role or license is present.

Capture the event before it changes

Save the event’s details and the time you observed them. At minimum, record the user or workload identity, timestamp, application or client, target resource, status, authentication details, device, IP address, location, user agent, Conditional Access result, risk detections, and correlation ID. Also note whether the record came from an interactive or non-interactive user sign-in. If the incident involves an application identity, include service-principal or managed-identity activity.

Step 1: Establish the sign-in and the identity

In the Microsoft Entra admin center, open Monitoring & health > Sign-in logs. Start with the event that triggered the alert, then inspect the surrounding records for the same identity and period.

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Read the event across identity, client, and resource

Do not stop at “success” or “failure.” Read the event as a three-part relationship:

  • Identity: the user principal, service principal, or managed identity that initiated the request.
  • Client and authentication: the application, protocol or client type, device details, user agent, authentication methods attempted, and whether each step succeeded.
  • Target resource: the Microsoft 365 or directory resource requested.

Include both interactive and non-interactive user sign-ins. A legacy sign-in-log experience contains only interactive user sign-ins, so relying on that view can hide token-based or background activity. For workload identities, review the corresponding service-principal or managed-identity activity instead of forcing it into a human-user pattern.

Separate an authentication flow from an individual record

A user may have several records for one authentication attempt. For example, an MFA failure can be followed by a successful retry. The portal may merge those requests and show the final outcome, while Log Analytics retains multiple rows with the same correlation ID. Record the sequence and correlation ID before counting events; otherwise one attempted session can be mistaken for several independent sign-ins.

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Step 2: Compare the event with the user’s normal pattern

“Unfamiliar” is meaningful only against a baseline. Review earlier activity for the same identity and compare the application, device registration or compliance state, location, IP address, user agent, authentication sequence, and Conditional Access outcomes.

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Build a practical baseline

  • List the applications and target resources the user normally accesses.
  • Check whether the device is known, registered, and compliant when policy requires it.
  • Compare the network and IP history, including whether the user routinely works through a corporate VPN or mobile connection.
  • Compare user-agent and client changes. A new browser or protocol can be legitimate, but it deserves an explanation.
  • Review the order of authentication methods and the policies that allowed or blocked each attempt.
  • Normalize timestamps to one time zone before comparing events. The Entra admin center displays time localized to the viewer’s time zone, not necessarily the affected user’s.

Interpret risk detections as leads

Related detections can include impossible or atypical travel, anonymous or malware-linked IP addresses, a suspicious browser, password spraying, token anomalies or replay, unfamiliar sign-in properties, and suspicious inbox manipulation. These detections help you decide what to examine next; they do not, by themselves, establish what happened in your tenant. Look for corroboration in the authentication sequence, device, user history, and post-sign-in activity.

Step 3: Treat IP location as supporting evidence, not a verdict

Microsoft’s Entra sign-in guidance states: “There’s no definitive connection between an IP address and where the computer with that address is physically located.” Mobile providers can route traffic through distant address pools, and VPNs can make a connection appear to originate far from the user. IP-to-location data is therefore a best-effort estimate.

Use the reported country or city to generate a question, not a conclusion. Compare it with the device, application, protocol, user history, exact timestamps, and other signals. A new country combined with an unknown device, an unfamiliar client, and a successful password-only flow is more concerning than the same country on a known managed device using the organization’s VPN. Document the uncertainty in the case record rather than labeling the event malicious solely because the map looks wrong.

Step 4: Expand from sign-ins to audit and resource activity

A sign-in tells you how access began. Audit and resource records help determine what the identity did next.

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Review directory changes in Entra audit logs

Entra audit logs cover directory operations such as user and group management. Search the period immediately before and after the sign-in for changes made by the identity, changes to the identity, and changes that could affect future access. Pay particular attention to administrative modifications and policy-related changes that could weaken controls or create persistence.

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Use the Microsoft 365 activity logs for the full service view

For the broader Microsoft 365 activity picture, inspect the activity logs in the Microsoft 365 admin center. Correlate those records with the sign-in’s application, resource, timestamp, and identity. Look for data downloads, mailbox or inbox manipulation, file access, sharing changes, and administrative operations that fit the resources shown in the sign-in record.

Entra audit logs and Microsoft 365 activity logs are related but distinct. Reviewing only one can miss the other half of the sequence. If the investigation concerns unusual employee behavior as well as account compromise, Microsoft Purview Insider Risk Management may provide related signals; treat that tooling as complementary to the sign-in and audit timeline.

Ask the two search-aligned questions

  • What is the sign-in pattern of this user? Use the baseline and authentication sequence to answer it.
  • What changes were made to the app? Use directory and Microsoft 365 activity to identify configuration, permission, or resource changes after access.

Step 5: Correlate records without double-counting

If the tenant routes activity to Azure Monitor Log Analytics, Microsoft Sentinel, or another SIEM, use the shared identifiers to assemble a timeline. Microsoft’s examples use the SigninLogs and AuditLogs tables to filter risky sign-ins and summarize audit operations.

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Start with a narrow time window

  1. Set a window that begins before the reported sign-in and ends after the last relevant audit or resource event.
  2. Filter for the affected identity and inspect SigninLogs for status, application, resource, IP, risk information, and correlation ID.
  3. Group records by correlation ID before counting sessions. Keep failed and successful steps in sequence.
  4. Search AuditLogs for operations by the same identity and summarize the operation names and timestamps.
  5. Join the sign-in timeline to Microsoft 365 activity records using the identity, resource, and normalized time. Investigate gaps instead of assuming that an absent record proves no activity occurred.

Illustrative KQL starting points

The following patterns reflect the tables and analysis described in Microsoft guidance. Adjust field names and risk-value filters to the schema and connector version in your tenant.

SigninLogs
| where TimeGenerated between (datetime(2026-10-16T00:00:00Z) .. datetime(2026-10-16T23:59:59Z))
| summarize Records=count(), Apps=make_set(AppDisplayName), Outcomes=make_set(ResultType)
    by UserPrincipalName, IPAddress, CorrelationId
AuditLogs
| where TimeGenerated between (datetime(2026-10-16T00:00:00Z) .. datetime(2026-10-16T23:59:59Z))
| summarize Operations=count() by OperationName, InitiatedBy, bin(TimeGenerated, 1h)

These queries organize records; they do not determine whether the activity was malicious. Preserve the raw records and the query time range so another analyst can reproduce the timeline.

Step 6: Validate the activity through a trusted channel

When practical, ask the account holder whether they recognize the application, device, approximate time, and network. Confirm the timestamp after converting it to the user’s local time, and ask about travel, VPN use, mobile connectivity, and any MFA prompts.

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Do not assume that email or Teams is a trusted verification channel: those services may themselves be compromised. Use a channel that is independent of the potentially affected account, and document who confirmed what. A user’s denial is an important signal, but it should be weighed with the technical evidence rather than treated as conclusive on its own.

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Step 7: Contain suspected compromise and record the disposition

Choose the least disruptive action that matches the evidence and your incident procedure. If risk-based self-remediation is available, use it when appropriate. Otherwise, the response may include:

  • Resetting the password through an approved administrative process.
  • Re-registering MFA when the authenticator or its registration may be compromised.
  • Blocking the account while the investigation proceeds.
  • Revoking sessions or refresh tokens so previously issued access is no longer trusted.

Coordinate these steps with the identity owner and incident-response team; a password reset alone may not address a stolen session or a changed MFA registration. Preserve the evidence before destructive changes where your procedure allows, and record the exact time and operator for every containment action.

Close the investigation with an evidence-based status

After containment and review, mark the user or sign-in as confirmed compromised, confirmed safe, or risk dismissed when the evidence justifies that decision. Log the SOC actions, including policy changes, account blocks, unblocks, resets, MFA actions, and session revocation. If a user was unblocked or a policy was changed during response, record why and by whom.

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How to compare two suspicious events consistently

When several events involve one account or multiple related accounts, compare the same dimensions instead of relying on visual impressions in the portal.

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Dimension What to record Why it matters
Identity User, service principal, or managed identity Human and workload identities have different normal patterns and controls.
Application and resource Client application and target resource Shows what access path was used and what the request attempted to reach.
Outcome and sequence Success or failure, MFA steps, retries, and policy results Separates one multi-step authentication flow from several sessions.
Conditional Access Policies evaluated and their outcomes Explains why a request was allowed, challenged, or blocked.
Device Registration, compliance, and device familiarity Connects the request to an endpoint the organization recognizes.
Network IP address and cautiously interpreted location Provides context without treating geolocation as physical proof.
User agent Browser, client, or protocol string Highlights unexpected software or access methods.
Time Timestamp normalized to a common time zone Prevents viewer-localized portal times from creating false gaps.
Risk Risk detections attached to the event Supplies investigative leads that require corroboration.
Correlation Correlation ID and related log rows Prevents double-counting retries and MFA steps.
Aftermath Directory, Microsoft 365, data, and administrative activity Shows what the identity did after authentication.

Compare each event with the account’s own history and, where useful, with related users or events. Similarity to another account is context, not proof that the same person or actor is involved.

Common investigation mistakes and their fixes

Calling an unfamiliar country a compromise

Why it fails: VPNs and mobile networks can place the apparent IP far from the user. Fix: corroborate with device, client, protocol, user history, timestamps, and post-sign-in activity.

Relying only on the legacy sign-in view

Why it fails: that experience contains only interactive user sign-ins. Fix: include non-interactive records and workload-identity activity when relevant.

Counting every Log Analytics row as a login

Why it fails: one authentication flow can create multiple rows, such as an MFA failure followed by a successful retry. Fix: group by correlation ID and reconstruct the sequence.

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Stopping after a risk alert

Why it fails: a detection is a lead, not a tenant-specific account of what happened. Fix: inspect the baseline, authentication details, Conditional Access, and related audit or resource activity.

Verifying through a possibly compromised mailbox

Why it fails: email or Teams may be controlled by the same attacker. Fix: use an independent trusted channel and record the confirmation.

Assuming missing records prove no activity

Why it fails: retention, licensing, routing, and connector configuration affect what is available. Fix: document the tenant’s retention and access limits, then state conclusions only as strongly as the surviving evidence permits.

When the records cannot answer the question

No workflow can determine whether a particular sign-in was malicious, what data was accessed, or whether the tenant retained every necessary record without examining that tenant’s evidence. State those limits plainly. If a log is absent, identify whether the cause may be retention, filtering, delayed ingestion, an unconnected workload, or a portal view that excludes non-interactive activity. Keep the distinction between “not observed” and “did not happen.”

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For ongoing investigations, centralizing sign-in and audit data in Azure Monitor Log Analytics, Microsoft Sentinel, or another SIEM can make correlation and retention more consistent. Centralization does not replace checking source records, correlation IDs, portal time zones, and the identity’s baseline.

A concise analyst checklist

  • Open Monitoring & health > Sign-in logs and capture the complete event details.
  • Identify whether the actor is a user, service principal, or managed identity.
  • Include interactive and non-interactive records, not only the legacy interactive view.
  • Compare application, resource, device, IP, location, user agent, authentication sequence, and Conditional Access with the normal baseline.
  • Interpret risk detections as leads and IP geography as an estimate.
  • Normalize timestamps to one time zone and preserve the viewer-time-zone caveat.
  • Review Entra audit logs and the Microsoft 365 admin center activity logs.
  • Check data access, downloads, inbox manipulation, and administrative changes after the sign-in.
  • Use correlation IDs before counting Log Analytics rows as sessions.
  • Validate with the account holder through an independent trusted channel.
  • Contain when warranted through self-remediation, password reset, MFA re-registration, blocking, and session revocation.
  • Record the disposition, SOC actions, policy changes, and any unblock decision.

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